Often regarded as one of the most successful playwrights of the mid-twentieth century, Lillian Hellman also led one of the most colorful lives. Born in New Orleans in 1905 to a Jewish family, Hellman spent brief stints at NYU and Columbia University before dropping out. She toured Europe in 1929, getting an early glimpse of Nazism and socialism. She would become a lifelong anti-fascist and unrepentant leftist, and found herself on the blacklist during the McCarthyism era.

In 1930, Hellman found herself in Hollywood, where she met and fell in love with Dashiell Hammett, who pioneered the detective novel with The Maltese Falcon (1929). They remained together, unmarried, until Hammett’s death from lung cancer in 1961. Many believe that Hammett’s The Thin Man (1934) captures their witty, booze-drenched relationship. Perhaps not coincidentally, there are a Nick and a Nina in The Autumn Garden, though they are a world away from Hammett’s light-hearted Nick and Nora Charles.

Hellman’s first play, The Children’s Hour (1934), was an instant succès de scandale with its daring depiction of lesbianism. She returned periodically to the stage, with a series of rich and well-constructed plays. Many of them can be traced back to her biography, such as The Little Foxes (1939) and Another Part of the Forest (1946). The Autumn Garden (1951), is set in a New Orleans boarding-house exactly like the one owned by Hellman’s aunts, where she spent her youthful summers.

Hellman’s plays were usually tightly plotted, turning on secrets to be revealed. But The Autumn Garden forsakes this relentless narrative advance, opting instead for an elliptical structure recalling Chekhov. The story is simple, but the texture is thick: Mad Men on a manse. Hellman creates intricate, eerily lifelike scenes in which all of the characters struggle to articulate a nagging feeling of disappointment.

At its best, the play depicts mismatched couples trying to make sense of life and love. Nick, the narcissistic artist, is paired with Nina, the adoring society wife who enables his profligate lifestyle. The terse, wry army general Benjamin Griggs is paired disastrously with Rose, a former southern belle who compulsively casts herself in melodramatic scenes. Hellman also gives us an oblique self-portrait in Constance Tuckerman, who like the boarding-house she owns, has lost some of her luster. Ned Crossman, the charming drinker, now weary of life, could be read as a furtive depiction of her beloved Dash, to whom the play is dedicated.

Though the play is set in summer, this is a decidedly autumnal garden: nearly all of the characters are middle aged, and filled with regret for their youthful, romantic selves. The only young people in the play don’t have that luxury: Freddy is a closeted homosexual engaged to Sophie, Constance’s niece from France, who has lived through more hardship than all of the self-absorbed Americans put together. On the other end of the age spectrum is another truth-teller: Mrs. Ellis, a southern dowager with a Bracknellian bark and a Lady M bite.

In The Autumn Garden, Chekhovian pathos takes on an unmistakably American tone. Hellman’s characters mix wit and pain with hardscrabble observation. Hellman often called The Autumn Garden her favorite of her plays. It is revered among theatre people as a test: the one in which her artistry reaches a peak, and also the one most difficult to stage well.